CN104193691B - The synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof - Google Patents
The synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof Download PDFInfo
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- CN104193691B CN104193691B CN201410461905.9A CN201410461905A CN104193691B CN 104193691 B CN104193691 B CN 104193691B CN 201410461905 A CN201410461905 A CN 201410461905A CN 104193691 B CN104193691 B CN 104193691B
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- 150000001412 amines Chemical class 0.000 title claims abstract description 49
- 238000010189 synthetic method Methods 0.000 title claims abstract description 28
- 229910052793 cadmium Inorganic materials 0.000 title claims abstract description 14
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- -1 amine cadmium complexes Chemical class 0.000 claims abstract description 17
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 229960004643 cupric oxide Drugs 0.000 claims abstract description 7
- 150000003852 triazoles Chemical class 0.000 claims abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 4
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 10
- 239000013078 crystal Substances 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses the synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof, relate to field of light emitting materials.The synthetic method of three-(4-triazol radical phenyl) amine take cupric oxide as catalyzer, take methyl-sulphoxide as solvent, be under the condition of 120 ~ 170 DEG C, three-(4-iodobenzene) amine and triazole are reacted in temperature, then obtain three-(4-triazol radical phenyl) amine through solvent cut, filtration, decolouring, separating-purifying successively; The synthetic method of cadmium complex is by water-soluble with in the mixing solutions of alcohol after the mixing of 5-amino isophthalic acid, three-(4-triazol radical phenyl) amine and cadmium acetate, stir under acid or neutral condition afterwards and obtain reaction solution, this reaction solution is loaded in reactor and carries out crystallization reaction to three-(4-triazol radical phenyl) amine cadmium complexes.This synthetic method obtains crystal purity by simple synthetic route and is greater than 95%, three-(4-triazol radical phenyl) amine and cadmium complex thereof that productive rate is greater than 85%.
Description
Technical field
The present invention relates to field of light emitting materials, be specifically related to the synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof.
Background technology
In recent years, by metal ion with have machine multifunctional nitrogenous or form title complex to construct and have containing carboxylic-acid part the great interest that novel entanglement emitting complexes material has caused people, not only because they have novel charming topology network architecture, and mainly because they are subject to the people's attention in optical pickocff, photophore or the potential application in magneticsubstance etc.But design and construct this kind of luminescent material with special construction and performance there is very large challenge, particularly there is the functional complexes material of tangled structure.Up to now, this type of bibliographical information with the luminescent material of tangled structure is also relatively less.
Summary of the invention
The object of the present invention is to provide the synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof, this title complex is the three-dimensional net structure with tangled structure feature, can be used as fluorescent probe and has potential using value.
Object of the present invention can be achieved through the following technical solutions:
A kind of synthetic method of three-(4-triazol radical phenyl) amine, the method take cupric oxide as catalyzer, take methyl-sulphoxide as solvent, be under the condition of 120 ~ 170 DEG C, three-(4-iodobenzene) amine and triazole are reacted in temperature, then obtain three-(4-triazol radical phenyl) amine through solvent cut, filtration, decolouring, separating-purifying successively; Wherein, the chemical formula of three-(4-triazol radical phenyl) amine is C
24h
18n
10.The structural formula of three-(4-triazol radical phenyl) amine is such as formula shown in I:
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine, three-(4-iodobenzene) amine: triazole: the mol ratio of cupric oxide is 10:35 ~ 45:1; In the synthetic method of preferred three-(4-triazol radical phenyl) amine, three-(4-iodobenzene) amine: triazole: the mol ratio of cupric oxide is 10:35:1.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine, three-(4-iodobenzene) amine: the mol ratio of methyl-sulphoxide is 1:2 ~ 2.5.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine, the temperature of preferred reaction is 150 ~ 160 DEG C.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine, solvent cut solvent used is any one in methyl alcohol, ethanol, ethyl acetate, methylene dichloride and trichloromethane; It is methyl alcohol that preferred solvent dilutes solvent used.
A kind of synthetic method of three-(4-triazol radical phenyl) amine cadmium complexes, the method is by water-soluble with in the mixing solutions of alcohol after the mixing of 5-amino isophthalic acid, three-(4-triazol radical phenyl) amine and cadmium acetate, stir under acid or neutral condition afterwards and obtain reaction solution, loaded in reactor by this reaction solution and carry out crystallization reaction (crystallization), filtration after reaction, washing and drying obtain three-(4-triazol radical phenyl) amine cadmium complexes; Wherein the structural formula of three-(4-triazol radical phenyl) amine cadmium complexes is such as formula shown in II:
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine cadmium complex, described neutrality or the condition of acidity refer to that pH value is 6 ~ 7.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine cadmium complex, the mol ratio of 5-amino m-phthalic acid, three-(4-triazol radical phenyl) amine and cadmium acetate is 1.5 ~ 2:1:1.5.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine cadmium complex, three-(4-triazol radical phenyl) amine: the mass ratio of the mixing solutions of water and alcohol is 1:2 ~ 3; Wherein, in described water and the mixing solutions of alcohol, the mass ratio of water and alcohol is 1:2, and described alcohol is methyl alcohol or ethanol.
In the synthetic method of three described in technical solution of the present invention-(4-triazol radical phenyl) amine cadmium complex, the condition of crystallization reaction is reacted 72 hours under temperature is 140 ~ 160 DEG C of conditions; The condition of preferred crystallization reaction is reacted 72 hours under temperature is 150 DEG C of conditions.
Beneficial effect of the present invention:
The invention provides the synthetic method of a kind of three-(4-triazol radical phenyl) amine and cadmium complex thereof, this synthetic method obtains crystal purity by simple synthetic route and is greater than 95%, three-(4-triazol radical phenyl) amine and cadmium complex thereof that productive rate is greater than 85%.This inventive method synthesizes three-(4-triazol radical phenyl) the amine cadmium complexes prepared can produce fluorescence and to cobalt, nickel metal ion has Fluorescence Increasing or quenching effect, this title complex can be used as the luminescent material preparing fluorescent probe simultaneously, for some metal ion in testing environment or food, its detection method is simple, selectivity is higher, have broad application prospects, along with continuous progress and the fast development of luminescent material technology, it provides opportunity to develop not only can to type material engineering and type material synthesis, more can in raising Energy efficiency, reduce manufacturing cost, advocate energy-saving and emission-reduction, there is great meaning the aspects such as creation environment friendly society.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but protection scope of the present invention is not limited thereto:
Embodiment 1
The synthesis of three-(4-triazol radical phenyl) amine:
Be under the condition of 150 DEG C in temperature, getting 0.8g (0.01mol) cupric oxide is catalyzer, 19.5g (0.25mol) methyl-sulphoxide is solvent, the triazole of three of 62.3g (0.1mol)-(4-iodobenzene) amine and 24.2g (0.35mol) is reacted, the time of reaction is 24 hours, after reaction terminates, reaction soln diluted through methanol solution successively, filter, decolour, it is 96% that last separating-purifying obtains purity, and productive rate is three-(the 4-triazol radical phenyl) amine of 88.6%.Fig. 1 is the infrared spectrogram of three-(4-triazol radical phenyl) amine.
HRMS (ESI-TOF) (m/z): calculated value: [M+H]
+446.17, measured value: 446.15.
The synthesis of three-(4-triazol radical phenyl) amine cadmium complexes:
By 5-amino isophthalic acid 27.15g (0.15mol), three-(4-triazol radical phenyl) amine 44.98g (0.1mol) and cadmium acetate 34.5g (0.15mol) joins in the mixed solution of water and alcohol, wherein the quality of water is 36.2g, the quality of methyl alcohol is 72.4g, regulate pH value to 6 ~ 7 of reaction solution afterwards, stir 30 minutes, obtain mixing solutions: loaded by above-mentioned mixing solutions in reactor, under temperature is 150 DEG C of conditions between crystallization inverse time 72 hours, room temperature is naturally cooled to after reaction, the water white transparency shape crystal obtained after filtering solution, namely three-(4-triazol radical phenyl) amine cadmium complexes are prepared, finally wash to plane of crystal inclusion-free with methyl alcohol or ethanolic soln, this entanglement emitting complexes can be obtained after drying, the purity of the title complex prepared is 96.1%, yield is 89.3%.This title complex is the entanglement three-dimensional net structure with rotaxane feature, and complex crystal belongs to oblique system, and spacer is p21/n, unit cell parameters is: a=10.1482, b=32.5446, c=10.3533, α=γ=90.0000, β=106.6092, V=3276.7183.In crystal, have the rotaxane feature that poly-line is worn, be three-dimensional network tangled structure.Fig. 2 is the infrared spectrogram of three-(4-triazol radical phenyl) amine cadmium complexes.
Made by Fig. 3 three-(4-triazol radical phenyl) amine and three-(4-triazol radical phenyl) amine cadmium complexes all have fluorescent characteristic.Wherein, three-(4-triazol radical phenyl) amine cadmium complexes are under the exciting of 295nm wavelength, luminous at 417nm wavelength place.
Claims (7)
1. the synthetic method of one kind three-(4-triazol radical phenyl) amine, it is characterized in that: the method take cupric oxide as catalyzer, take methyl-sulphoxide as solvent, be, under the condition of 120 ~ 170 DEG C, three-(4-iodobenzene) amine and triazole are reacted 24 hours in temperature, then obtain three-(4-triazol radical phenyl) amine through solvent cut, filtration, decolouring, separating-purifying successively, the structural formula of three-(4-triazol radical phenyl) amine is such as formula shown in I:
Wherein: three-(4-iodobenzene) amine: triazole: the mol ratio of cupric oxide is 10:35 ~ 45:1; Three-(4-iodobenzene) amine: the mol ratio of methyl-sulphoxide is 1:2 ~ 2.5; Solvent cut solvent used is any one in methyl alcohol, ethanol, ethyl acetate, methylene dichloride and trichloromethane.
2. the synthetic method of three-(4-triazol radical phenyl) amine according to claim 1, is characterized in that: the temperature of reaction is 150 ~ 160 DEG C.
3. the synthetic method of one kind three-(4-triazol radical phenyl) amine cadmium complex, it is characterized in that: the method is by 5-amino isophthalic acid, it is water-soluble with in the mixing solutions of alcohol after three-(4-triazol radical phenyl) amine and cadmium acetate mix, stir under neutral or acid condition afterwards and obtain reaction solution, this reaction solution is loaded in reactor and carries out crystallization reaction, filter after reaction, washing and drying obtain three-(4-triazol radical phenyl) amine cadmium complexes, wherein the structural formula of three-(4-triazol radical phenyl) amine cadmium complexes is such as formula shown in II:
4. the synthetic method of three-(4-triazol radical phenyl) amine cadmium complexes according to claim 3, is characterized in that: neutral or acid condition refers to that pH value is 6 ~ 7.
5. the synthetic method of three-(4-triazol radical phenyl) amine cadmium complexes according to claim 3, is characterized in that: the amino m-phthalic acid of 5-: three-(4-triazol radical phenyl) amine: the mol ratio of cadmium acetate is 1.5:1:1.5.
6. the synthetic method of three-(4-triazol radical phenyl) amine cadmium complexes according to claim 3, is characterized in that: three-(4-triazol radical phenyl) amine: the mass ratio of the mixing solutions of water and alcohol is 1:2 ~ 3; Wherein, in described water and the mixing solutions of alcohol, the mass ratio of water and alcohol is 1:2, and described alcohol is methyl alcohol or ethanol.
7. the synthetic method of three-(4-triazol radical phenyl) amine cadmium complexes according to claim 3, is characterized in that: the condition of crystallization reaction is reacted 72 hours under temperature is 140 ~ 160 DEG C of conditions.
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